Tetrahydrofuran → HCID 44224242, compound

HRID 1477201Notes

Reaction equation

HRID 1477201 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7][C:6]([N:15]([CH3:24])[C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[CH2:16]([N:15]([CH3:24])[C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:8][C:3]([N:2]([CH3:31])[CH3:1])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:4][CH2:5]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 68631670N-(4-dimethylamino-1,4-diphenyl-cyclohexyl)-N-methyl-benzamide

Product 1

HCID 44224242HCID 44224242, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound from step 1 (160 mg, 0.387 mmol) was dissolved in abs. THF (15 mL) and mixed with LiAlH4 (29 mg, 0.775 mmol) in argon. The batch was boiled for 7 h with reflux and then cooled to room temperature. THF (5 mL) and H2O (5 mL) were added to the batch with ice cooling and subsequently stirred for 30 min. The batch was filtered over a fritted glass filter with diatomaceous earth and subsequently rinsed with dichloromethane (50 mL). The combined filtrates were concentrated to low volume in vacuum.

Workup

  1. temperaturewith reflux
  2. filtrationThe batch was filtered over a fritted glass
  3. filtrationfilter with diatomaceous earth
  4. washsubsequently rinsed with dichloromethane (50 mL)
  5. concentrationThe combined filtrates were concentrated to low volume in vacuum

Sources & evidence

ORD record
ord-0c9c6374d3f84d78a66b60064c106005
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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